B-alkylamino-ethylaminobenzoic alkyl esters and their derivatives



' UNrTEn sTA ns PATENT orrron.

man nmwneo AND JOANNY munmvon onmroun nns usnmsmr mom: (ANC TIER), 0]! PABIS, FRANCE.

, or LYON, FRANCE, ASSIGNORS 'ro socm'rn IENNEMENT GILLIARD P. uomm'r ET can B-ALKYLAMINO-ETHYLAMINOBENZOIG ALKYL ESTERS AND THEIR DERIVATIVES.

1,334,642. no Drawing nguon on uno npoon where It represents ether a hydrogen atom oran alkyl radical, and R an alkyl radical. According to this invention (S-alkylaminoethylamino-benzoic alkyl esters can be obtained by heating for several hours in a closed vessel at a temperature of approximately 100 C. a mixture of an alkylamin and of a (5-halogen-ethyl-aminobenzoic ester having the general formula wCH CH NHC ILOOOR where a: represents a halogen and R an alkyl radical. The new esters obtained in this manner occur as oils insoluble in water. Their mono-hydrochlorids can be obtained by addition of hydrochloric acid in equal molecular proportion. The latter salts are easily crystallized and are very soluble in water with which they form neutral solutions. 4 h

Example I: A mixture of two molecules of diethylamin and one molecule of ethyl chlorethyl p amino benzoate having the formula CICH,CH,NHC,H,COOC,H, is heated for several hours at a tem rature of approximately 100 in a close vessel.

After cooling a crystalline mass is obtained which is treated with water, to eliminate the diethylamin hydrochlorid resulting from th r c i n- Th new est r separates as a Specification of Letters Patent.

Patented Mar. 23, 1920.

Application filed June 13, 1919. send No. 303,974.

oily liquid, and is the ethyl {5-diethyl-aminoethylamino benzoate having the formula (C H,) NGH CH NHC H COOC,H

It'is washed with water and decanted. In order to obtain the mono-hydrochloridit sufiices to dissolve the eth 1 (i-diethyl-aminoethylamino benzoate in ilute hydrochloric acid in theoretical pro ortion and to evap-. crate to dryness. A ter recr stallization from alcohol white needles wit a melting point of 156C. are obtained.

Example II: Admixture of one molecule of {5- chlorethyl paramino benzoate of normal butyl and two molecules of diethylamin bath. After heating for 10 hours, the resulting products are cooled and treated with cold water. The diethylamino-ethyl-paramino benzoate of normal butyl separates in the form of oil, and this oil is washed with water and distilled under reduced pressure, the principal fraction distilling over at 213-214, under 6 mm. of mercury. In order to obtain the monochlorhydrate of this ether-base, one operates as indicated in Example I. This monochlorhydrate melts at v127, and is soluble in water with a neutral reaction. It is fairly'soluble in ethyl and methyl alcohol, less soluble in acetone, little soluble in benzin. j

I Example III: In replacing in Example II the two molecules of diethylamin by two molecules of monomethylamin, one obtains, in operating similarly, as an ether-base, the mono (5 -.methylamino-ethyl paramino benzoate of normal butyl, in the form of an alkaline oil distilling at 214? under a pressure v is heated in a closed vessel on the water of 6 mm. of mercury. Its monochlorhydrate melts at 141.

It is understood that the above examples are given by way of illustrative example only, and may be varied in details according to the particular reagents employed.

What we claim and desire to secure by Letters Patent is 1. The new industrial products the B-alkyl a ia t y e ia -bee de a la'l which may be obtained by the above de- In witness whereof we have hereunto 10 scribed process, being oils insoluble in si%ned our names in the presence of two wateri h d h y su scribing witnesses.

2. e new in ustrial products, t e mono- 5 hydrochlorids of -alkylzunino-ethy1aminobenzoic alkyl ester which may be obtained by i the above described process being crystalline Witnesses:

salts, very soluble in water with which they MARIN VACHON,

form neutral solutions. LOUIS Escmm. 

